1: conc. H2SO4 / benzene / 3 h / Heating 2: 1.) diisobutylaluminum hydride, 2.) conc. HCl / 1.) toluene, hexane, -78 deg C, 1.5 h, 2.) THF, -78 deg C, 5 min 3: 1.) n-BuLi/N-isopropylcyclohexylamine / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, -78 deg C, 2 h 4: bromine, triphenyl phosphite / benzene / 1 h / Ambient temperature 5: sodium borohydride, tri-n-butyltin chloride / ethanol / 1.) room temp., 30 min, 2.) reflux, 45 min 6: KOH / ethanol / 1 h / Heating 7: 84 percent / HF (g) View Scheme

1: conc. H2SO4 / benzene / 3 h / Heating 2: 1.) diisobutylaluminum hydride, 2.) conc. HCl / 1.) toluene, hexane, -78 deg C, 1.5 h, 2.) THF, -78 deg C, 5 min 3: 1.) n-BuLi/N-isopropylcyclohexylamine / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, -78 deg C, 2 h 4: bromine, triphenyl phosphite / benzene / 1 h / Ambient temperature 5: sodium borohydride, tri-n-butyltin chloride / ethanol / 1.) room temp., 30 min, 2.) reflux, 45 min 6: KOH / ethanol / 1 h / Heating View Scheme

1: conc. H2SO4 / benzene / 3 h / Heating 2: 1.) diisobutylaluminum hydride, 2.) conc. HCl / 1.) toluene, hexane, -78 deg C, 1.5 h, 2.) THF, -78 deg C, 5 min 3: 1.) n-BuLi/N-isopropylcyclohexylamine / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, -78 deg C, 2 h 4: bromine, triphenyl phosphite / benzene / 1 h / Ambient temperature 5: sodium borohydride, tri-n-butyltin chloride / ethanol / 1.) room temp., 30 min, 2.) reflux, 45 min 6: KOH / ethanol / 1 h / Heating 7: 84 percent / HF (g) 8: 96 percent / sodium borohydride / ethanol / 1.83 h / 55 - 60 °C 9: 93 percent / glacial acetic acid, conc. HCl / 0.25 h 10: 60 percent / 10percent palladium on charcoal / 300 - 305 °C View Scheme

1: conc. H2SO4 / benzene / 3 h / Heating 2: 1.) diisobutylaluminum hydride, 2.) conc. HCl / 1.) toluene, hexane, -78 deg C, 1.5 h, 2.) THF, -78 deg C, 5 min 3: 1.) n-BuLi/N-isopropylcyclohexylamine / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, -78 deg C, 2 h 4: bromine, triphenyl phosphite / benzene / 1 h / Ambient temperature 5: sodium borohydride, tri-n-butyltin chloride / ethanol / 1.) room temp., 30 min, 2.) reflux, 45 min 6: KOH / ethanol / 1 h / Heating 7: 84 percent / HF (g) 8: 96 percent / sodium borohydride / ethanol / 1.83 h / 55 - 60 °C View Scheme

暂无反应条件数据

1: conc. H2SO4 / benzene / 3 h / Heating 2: 1.) diisobutylaluminum hydride, 2.) conc. HCl / 1.) toluene, hexane, -78 deg C, 1.5 h, 2.) THF, -78 deg C, 5 min 3: 1.) n-BuLi/N-isopropylcyclohexylamine / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, -78 deg C, 2 h 4: bromine, triphenyl phosphite / benzene / 1 h / Ambient temperature 5: sodium borohydride, tri-n-butyltin chloride / ethanol / 1.) room temp., 30 min, 2.) reflux, 45 min 6: KOH / ethanol / 1 h / Heating 7: 84 percent / HF (g) 8: 96 percent / sodium borohydride / ethanol / 1.83 h / 55 - 60 °C 9: 93 percent / glacial acetic acid, conc. HCl / 0.25 h View Scheme

hydrogenchloride in acetic acid 8 h; Heating;

1,2-dichloro-benzene T=180 - 190°C;

sulfuric acid in benzene Yield given;

1: H2SO4 / benzene 2: 75 percent / NaOEt / ethanol / 18 h / Heating View Scheme